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For more information please read our cancellation policy and terms and conditions page or call our staff with any questions regarding your ability to participate. However, you won’t have a full half day in the water on this cruise (like other snorkel trips), since the entire cruise is 3 hours long. You can expect to pay between $50 – $100 per person for a sunset cruise in Key West. Almost every single sunset cruise in Key West will leave from the Key West Historic Seaport shown in the map below.
Top Key West Sunset Cruises
To watch the sun dip below the dark blue waters from a luxurious Best on Key West boat, all while sailing through the warm breeze along the southernmost point of the continental United States, is truly a spectacular venture. Don’t miss out on making some the greatest memories with the ones you love under the best views of the Key West sunset skies. Come sail along on an ocean breeze and enjoy some of Key West’s best musicians performing live to the backdrop of the setting sun. You’ll eat, drink and party the night away on Key West’s original live music sunset sail. So, grab someone’s hand and let the music move you as we chase down the world famous Key West sunset. Skipjack schooners were originally designed for harvesting oysters in shallow Chesapeake Bay.
COMMOTION ON THE OCEAN KEY WEST SUNSET SAIL with LIVE MUSIC
There are usually 4 red and 3 white wines plus a champagnoise open for the tasting. The charcuterie and cheese board goes far beyond simple sailors’ rations to deliver the perfect wine pairings with Dill Havarti, Smoked Gouda, fresh Mozzarella, and Brie cheeses. Caprese skewers, summer sausage, honey-drizzled green apple slices, fruit, water crackers and more make for the ultimate water-borne wine tasting session. The custom of celebrating the amazingly colorful ocean sunsets took hold, and now Mallory Square and the Key West sunsets are both world famous. We love both public and private cruises, as we enjoy getting to know our guests.
Key West Sunset Cruises
This seaport is just outside of historic Old Town, so if you are staying nearby, walking shouldn’t be a problem. If the activity must is cancelled due to bad weather, and you cannot reschedule, you will be issued a full refund. Our sailing adventures begin off the docks located behind local-favorite Schooner Wharf bar. I’ve seen people in jean shorts and flip flops, but most people dress in resort casual. Unfortunately, we are not able to provide alternative menu items for those patrons who adhere to a specific diet or those susceptible to food allergies.

Depart the harbor in the late afternoon to enjoy an evening on the water, or combine dolphin watching, snorkeling, or a glass-bottom boat tour with sunset and the perfect end to another day in paradise. Key West sunsets are famous for highlighting nature’s grandeur as the sun sinks below the broad ocean horizon and brings on dramatic color changes of a range and intensity not seen on land. The unobstructed fetch of the light, atmospheric moisture, and other refractory factors combine to produce awe-inspiring natural beauty. This catamaran sunset sail is consistently voted one of the best sunset cruises in Key West. As you sail off into the sunset on our luxury catamaran, grab a tropical mixed drink and dance the night away to a live performance from one of Key West’s best entertainers while enjoying the legendary Key West sunset.
Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar

In my opinion, one of the best things to do in Key West is go on a sunset cruise. In fact, Key West sunsets are so legendary, they have a nightly festival to watch them from Mallory Square. However, we limit our cruises to approximately 26 passengers, so it’s never crowded. That way, our roomy decks allow for plenty of seating, and for you to walk around and explore the ship while sailing.
How To Spend A Memorable Day In Key West Cruise Port - TravelAwaits
How To Spend A Memorable Day In Key West Cruise Port.
Posted: Mon, 16 Oct 2023 07:00:00 GMT [source]
Frequently Asked Questions
These classic ships have been sailing out of Key West for over 200 years, and guests who come aboard a Key West schooner today are in for an award-winning luxury sunset cruise. This trip also includes great appetizers for you to enjoy as you cruise off into the sunset through tropical waters aboard Key West’s newest sailing catamaran, The Sandie Cat. Looking to party with some reggae or just enjoy live music and a cocktail hour at sunset? The award-winning Key West Wind & Wine Sunset Sail is notable for its pairing of fine wines and craft beers with gourmet appetizers.
ABOUT THE BOAT
With quiet, unobstructed on-deck views, the blazing orange, red, and purple clouds along the horizon and the awesome disc of the sun visible as it slides out of sight captured attention very early on. Now, modern vessels are able to provide visitors with a nice range of specialized sunset-watching cruises to suit any taste, and the best way to find out why Key West Sunset Cruises are so special is to come aboard and try one (or more). We invite you to experience the sunset in true Key West fashion with your loved ones, friends or your whole family.
While aboard our schooner, you will see the sunset as it stretches across the sky and reflects onto the vast surface of the water, and finally disappearing down into the sea. This boat is equipped with a fully stocked bar so your guests can enjoy craft cocktails, draft beer and a selection of beer, wine & champagne. The Sandie Cat also has 2 above deck modern restrooms, an illuminated dance floor with cocktail tables, state of the art sound system, front deck and a top deck with the best view in town. For an active family, or anyone who enjoys the water, taking an afternoon snorkeling trip that winds down with a beautiful sunset (and beverages) offers the best of both worlds. Nature lovers should try a Glass-Bottom Boat Tour Sunset Combo or take the Dolphin Watch Sunset Snorkel Cruise. If you are planning a Key West vacation, you might wondering what you should in the evenings.
A private sail aboard Schooner Spirit of Independence creates the perfect venue for private events, weddings, corporate events, parties, and all types of social functions. Our professional crew make excellent hosts and will provide you and your guests with five-star service. If you search for Key West sunset cruises on TripAdvisor, this tour with Sebago Watersports is the most highly rated, with over 2000 reviews.
The steel hull makes her very stable – providing a smooth sailing experience, not a rocky boat ride. This triple level catamaran gives its guests plenty of room and options to get comfortable as you sail through the Key West waters. It is your responsibility to make sure you are aware of and understand all restrictions pertaining to this tour before booking online or over the phone. It is your responsibility to ensure that you are medically qualified and within any limits listed below in order to participate in this activity. No refunds will be given to those who reserve a spot and can not participate due to the restrictions listed below.
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